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WO2014061493A1 - Procédé permettant de fabriquer un dispositif électronique - Google Patents

Procédé permettant de fabriquer un dispositif électronique Download PDF

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Publication number
WO2014061493A1
WO2014061493A1 PCT/JP2013/077246 JP2013077246W WO2014061493A1 WO 2014061493 A1 WO2014061493 A1 WO 2014061493A1 JP 2013077246 W JP2013077246 W JP 2013077246W WO 2014061493 A1 WO2014061493 A1 WO 2014061493A1
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Prior art keywords
thin film
layer
organic
organic thin
electronic device
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English (en)
Japanese (ja)
Inventor
行一 六原
修一 佐々
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to EP13847203.0A priority Critical patent/EP2908608B1/fr
Priority to CN201380052889.1A priority patent/CN104718798B/zh
Priority to US14/434,518 priority patent/US9437821B2/en
Publication of WO2014061493A1 publication Critical patent/WO2014061493A1/fr
Anticipated expiration legal-status Critical
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    • H—ELECTRICITY
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    • H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
    • H10D30/00—Field-effect transistors [FET]
    • H10D30/60—Insulated-gate field-effect transistors [IGFET]
    • H10D30/67—Thin-film transistors [TFT]
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    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/52—Luminescence
    • C08G2261/522—Luminescence fluorescent
    • C08G2261/5222—Luminescence fluorescent electrofluorescent
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    • C08G2261/70—Post-treatment
    • C08G2261/76—Post-treatment crosslinking
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/95—Use in organic luminescent diodes
    • C—CHEMISTRY; METALLURGY
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    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
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    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to an electronic device manufacturing method and a thin film manufacturing method.
  • Organic electroluminescence elements sometimes referred to as organic EL elements
  • organic photoelectric conversion elements and organic thin film transistors
  • Such an electronic device may have a structure in which a plurality of layers including an organic thin film are laminated (hereinafter sometimes referred to as a laminated structure).
  • a process for forming an organic thin film in which a coating solution is applied to a predetermined region by a coating method such as an inkjet method, and this coating film is irradiated with a laser beam and dried. (See Patent Document 1).
  • a coating method when two or more layers (thin films) of a laminated structure provided between two or more electrodes are continuously formed by a coating method (the previously formed layer is called a lower layer, In some cases, another layer formed later so as to be bonded to the lower layer is referred to as an upper layer.)
  • a coating solution for forming the upper layer is applied to the surface of the lower layer. . In that case, a part or all of a lower layer may melt
  • a material having a crosslinkable group introduced is used, or a material containing a crosslinking agent is used to crosslink the lower layer components to solidify. can do.
  • a crosslinking reaction is performed by using a material into which a crosslinkable group is introduced or by performing a heat treatment using a crosslinking agent, a heat treatment for a long time is required.
  • the crosslinking reaction is carried out in a short time by irradiating strong light such as laser light, but in this case, the temperature of the substrate or the electrodes and functional layers already provided is excessive. As a result, the substrate may be deformed and the electrode or the functional layer may be damaged.
  • the present invention has been made in view of the above problems, and provides a method for manufacturing an electronic device and a method for manufacturing a thin film used in the electronic device that can suppress damage such as substrate deformation, electrode, and functional layer deterioration.
  • the purpose is to provide.
  • the present invention provides the following [1] to [8].
  • [1] A method for producing an electronic device having two or more electrodes and an organic thin film provided between the two or more electrodes, Applying a coating solution containing a material having a crosslinkable group to form a coating film; Forming the organic thin film by repeatedly irradiating the coating film with electromagnetic waves to crosslink the crosslinkable group.
  • the electromagnetic wave generation source is a xenon flash lamp.
  • the step of forming the organic thin film is a step of forming the organic thin film by repeatedly irradiating the electromagnetic wave through a filter having a wavelength of 400 nm or less and an electromagnetic wave transmittance of 10% or less.
  • [4] The method for manufacturing an electronic device according to any one of [1] to [3], wherein the electronic device is an organic electroluminescence element, an organic photoelectric conversion element, or an organic thin film transistor.
  • the step of forming the organic thin film prepares a flexible substrate wound on a winding roll, and winds the flexible substrate unwound from the winding roll on a winding roll.
  • the method for manufacturing an electronic device and the method for manufacturing a thin film of the present invention when forming a thin film by a coating method, the thin film is solidified in a short time, and damage to the substrate or the already provided electrodes and functional layers is reduced. As a result, the performance of the manufactured electronic device can be improved.
  • FIG. 1 is a graph (1) showing the characteristics of the filter used.
  • FIG. 2 is a graph (2) showing the characteristics of the filter used.
  • the method for producing an electronic device of the present invention is a method for producing an electronic device having two or more electrodes and an organic thin film provided between the two or more electrodes, and a coating liquid containing a material having a crosslinkable group.
  • Examples of the electronic device of the present invention include an organic EL element, an organic photoelectric conversion element, and an organic thin film transistor.
  • the organic thin film used in the electronic device of the present invention is suitably applied when a thin film is formed on the organic thin film by a coating method.
  • the organic thin film used for the electronic device of the present invention is, for example, an organic EL element, it can be suitably applied to a hole transport layer, a light emitting layer, an electron transport layer, etc. formed by a coating method.
  • it is a conversion element it can be suitably applied to a hole transport layer, an active layer, an electron transport layer, etc. formed by a coating method
  • it is an organic thin film transistor it is formed by a coating method. It can be suitably applied to layers, active layers, electron injection layers, and the like.
  • the “organic thin film provided between the electrodes” means an organic thin film arranged so as to be at least a part of a path of electrons or holes moving between the electrodes.
  • a coating solution is prepared.
  • the coating liquid contains at least a material that is a main component and a solvent.
  • the material that is the main component are a light emitting material when the electronic device is an organic EL element, a hole transport material, and a predetermined function of an organic thin film such as a photoelectric conversion material when the electronic device is an organic photoelectric conversion element. Materials for.
  • the material itself for expressing the predetermined function of the organic thin film does not have a crosslinkable group, and further includes a crosslinker as a material having a crosslinkable group, 2)
  • a crosslinker as a material having a crosslinkable group
  • Examples of coating methods for coating the prepared coating solution to form a coating film include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, and wire bar coating. Method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, and inkjet printing method.
  • the coating method can be carried out as a step of coating the coating liquid in an atmosphere at about normal pressure, or in an air atmosphere.
  • the generation source that emits electromagnetic waves may be a generation source that continuously emits electromagnetic waves at a constant intensity or a generation source that emits electromagnetic waves in a pulsed manner.
  • emitted from the said generation source is interrupted
  • the state where the coating film is irradiated with the electromagnetic wave and the state where the electromagnetic wave is not irradiated are alternately repeated.
  • a continuation of electromagnetic waves in a state in which electromagnetic waves are irradiated is referred to as one pulse. If the time width of one pulse (referred to as pulse width) is too long, the substrate or the like is excessively heated, and if it is too short, it is not sufficient for the crosslinking reaction, and the time required for the solidification process becomes too long. It is suitably 1000 ⁇ s, preferably 50 ⁇ s to 500 ⁇ s, more preferably 50 ⁇ s to 160 ⁇ s, and even more preferably 50 ⁇ s to 100 ⁇ s.
  • the repetition period is too long, the state in which the electromagnetic wave is not irradiated becomes short, the substrate or the like is excessively heated, and if it is too short, the time required for the solidification process becomes too long.
  • the energy of one pulse is excessively heated is too high substrate, sufficiently and it can not be said to too low, the crosslinking reaction, since the time required for the solidification step is too long, 0.1 J / cm 2 ⁇ 100 J / cm 2 is appropriate, and 0.5 J / cm 2 to 50 J / cm 2 is preferable.
  • pulse peak energy the peak energy of one pulse
  • the substrate and the like are excessively heated, and if it is too low, it is not sufficient for the crosslinking reaction, and the time required for the solidification process becomes too long.
  • the total energy of the electromagnetic wave is irradiated on any site is suitably be 100J / cm 2 ⁇ 10000J / cm 2, 500J / cm 2 ⁇ 5000J / cm 2 It is preferable that
  • the wavelength of the electromagnetic wave to be irradiated is not particularly limited, but considering that the function and properties of the formed thin film and other components are not impaired, the range of visible light to near infrared light (wavelength is about 400 nm to 1100 nm). (Range).
  • electromagnetic wave generation sources examples include laser light, xenon flash lamps, high-pressure mercury lamps, and halogen lamps.
  • a xenon flash lamp is preferably used.
  • a xenon flash lamp having a configuration disclosed in Japanese Patent Application Laid-Open No. 2003-338265 can be used as an electromagnetic wave generation source.
  • the step of forming the organic thin film is preferably a step of repeatedly irradiating the electromagnetic wave through a filter having a wavelength of 400 nm or less and an electromagnetic wave transmittance of 10% or less. If such a filter is used, the damage by the irradiation of the electromagnetic waves with respect to the component already provided can be suppressed.
  • An electronic device manufacturing method including a step of forming an organic thin film includes a step of forming two or more electrodes and a step of forming an organic thin film provided between the two or more electrodes.
  • the manufacturing method of an electronic device may have the process of forming thin films other than the organic thin film formed as mentioned above between two or more electrodes.
  • the step of forming the organic thin film provided between two or more electrodes may be performed by a so-called roll-to-roll method or may be performed by a sheet method.
  • the step of forming the organic thin film is performed in a process until the substrate fed from the winding roll on which the flexible substrate is wound is wound on the winding roll. That is, the process of forming the organic thin film provided between two or more electrodes can also be performed by a roll-to-roll method using a long flexible substrate.
  • the step of forming the organic thin film is performed by preparing a flexible substrate wound up by an unwinding roll or a long structure in which a flexible electrode or the like is formed on the flexible substrate. You may carry out, winding up the flexible substrate or the elongate structure unwound from the winding roll.
  • the organic thin film forming process by the roll-to-roll method is performed by first conveying a material having a crosslinkable group while continuously conveying a long flexible substrate stretched between an unwinding roll and a winding roll.
  • the coating liquid is continuously applied to the main surface of the flexible substrate exposed between the unwinding roll and the winding roll to form a coating film.
  • the coating film is repeatedly irradiated with electromagnetic waves to crosslink the crosslinkable groups and solidify to form an organic thin film.
  • the organic thin film is insolubilized with respect to the coating liquid applied to the surface of the film in a later step.
  • a further thin film may be continuously formed on the organic thin film having the crosslinkable group crosslinked.
  • the thin film is formed by a coating method, since the lower organic thin film is insolubilized, damage to the lower organic thin film caused by the coating liquid for forming the thin film can be reduced.
  • an organic thin film may be formed by a roll-to-roll method.
  • a flexible substrate in which electrodes are formed in advance is prepared, and one or a plurality of organic thin films are formed by a roll-to-roll method using the flexible substrate, and then the flexible substrate is formed at a predetermined portion.
  • an electrode may be formed by a single wafer method to produce an electronic device.
  • a long flexible substrate that can be suitably applied to a roll-to-roll method includes a film or a sheet made of a colorless and transparent resin.
  • the substrate is preferably an insulating substrate.
  • the resin used for such a substrate include polyethersulfone (PES); polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN); polyethylene (PE), polypropylene (PP), cyclic polyolefin, and the like.
  • Polyolefin resin Polyamide resin; Polycarbonate resin; Polystyrene resin; Polyvinyl alcohol resin; Saponified ethylene-vinyl acetate copolymer; Polyacrylonitrile resin; Acetal resin; Polyimide resin;
  • polyester resin and polyolefin resin are preferable because of high heat resistance, low coefficient of linear expansion, and low manufacturing cost, and polyethylene terephthalate and polyethylene naphthalate are particularly preferable.
  • these resins may be used alone or in combination of two or more.
  • a metal substrate such as aluminum and a glass substrate can be used.
  • the thickness may be reduced to the extent that flexibility is exhibited.
  • the thickness of the flexible substrate is not particularly limited.
  • the thickness of the flexible substrate can be appropriately set in consideration of stability during film formation.
  • the thickness of the flexible substrate is preferably in the range of 5 ⁇ m to 500 ⁇ m, more preferably in the range of 50 ⁇ m to 200 ⁇ m, and particularly preferably in the range of 50 ⁇ m to 100 ⁇ m.
  • the substrate When manufacturing an electronic device using a long flexible substrate or a long structure while being conveyed by a roll-to-roll method, the substrate may be heated excessively and bent when irradiated with electromagnetic waves constantly. In some cases, the functional layer constituting the structure is deteriorated. However, since the electromagnetic wave is repeatedly irradiated in the manufacturing method of the present invention, it is possible to suppress the occurrence of problems such as the bending of the substrate and the deterioration of the functional layer due to the irradiation of the electromagnetic wave.
  • the conventional heat treatment requires a long transport distance to secure the time required to complete the crosslinking reaction. End up.
  • a predetermined electromagnetic wave is repeatedly irradiated under a predetermined condition as in the production method of the present invention, the crosslinking reaction can be completed in a very short time without excessively raising the temperature of the already provided structure. . Therefore, the method for manufacturing an electronic device and the method for manufacturing a thin film used in the electronic device of the present invention can be suitably applied to a manufacturing method by a roll-to-roll method.
  • the organic EL device of this embodiment includes a laminated structure including an anode, a cathode, and a hole injection layer, a hole transport layer, and a light emitting layer disposed between these electrodes.
  • the coating film is formed by applying a coating liquid containing a material having a crosslinkable group in the hole transport layer forming step as described above.
  • An example will be described which includes a process and a process of forming an organic thin film by repeatedly irradiating a coating film with electromagnetic waves to crosslink a crosslinkable group.
  • Examples of the layer provided between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, a hole blocking layer, and the like.
  • the layer in contact with the cathode is referred to as an electron injection layer, and the layer excluding this electron injection layer is referred to as an electron transport layer.
  • the electron injection layer has a function of improving electron injection efficiency from the cathode.
  • the electron transport layer has a function of improving electron injection from the cathode, the electron injection layer, or the electron transport layer closer to the cathode.
  • the hole blocking layer is a layer having a function of blocking hole transport. In the case where the electron injection layer and / or the electron transport layer have a function of blocking hole transport, these layers may also serve as the hole blocking layer.
  • the hole blocking layer has a function of blocking hole transport can be confirmed, for example, by producing an organic EL element that allows only hole current to flow, and confirming the blocking effect by reducing the current value.
  • Examples of the layer provided between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer.
  • the layer in contact with the anode is called a hole injection layer.
  • the hole injection layer has a function of improving the hole injection efficiency from the anode.
  • the hole transport layer has a function of improving hole injection from the anode, the hole injection layer, or the hole transport layer closer to the anode.
  • the electron block layer has a function of blocking electron transport.
  • these layers may also serve as the electron blocking layer.
  • the electron blocking layer has a function of blocking electron transportation can be confirmed, for example, by producing an organic EL element that allows only electron current to flow, and confirming the effect of blocking electron transportation by reducing the measured current value. .
  • anode / light emitting layer / cathode b) anode / hole injection layer / light emitting layer / cathode c) anode / hole injection layer / light emitting layer / electron injection layer / cathode d) anode / hole injection layer / light emitting layer / Electron transport layer / electron injection layer / cathode e) anode / hole injection layer / hole transport layer / light emitting layer / cathode f) anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode g ) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode h) Anode / light emitting layer / electron injection layer / cathode i) Anode / light emitting layer / light emitting layer / light emitting layer / cathode
  • the organic EL device of the present embodiment may have a single light emitting layer or two or more light emitting layers.
  • structural unit A when the laminate disposed between the anode and the cathode is referred to as “structural unit A”, an organic EL device having two light emitting layers is provided. Examples of the structure include the layer structure shown in j) below. The two (structural unit A) layer structures may be the same or different. j) Anode / (structural unit A) / charge generation layer / (structural unit A) / cathode
  • the charge generation layer is a layer that generates holes and electrons by applying an electric field.
  • Examples of the charge generation layer include a thin film made of vanadium oxide, indium tin oxide (abbreviated as ITO), molybdenum oxide, or the like.
  • examples of the configuration of the organic EL element having three or more light-emitting layers include the layer configuration shown in the following k).
  • x represents an integer of 2 or more
  • stacked is represented.
  • a plurality of (structural units B) may have the same or different layer structure.
  • an organic EL element may be configured by directly laminating a plurality of light emitting layers without providing a charge generation layer.
  • the organic EL element having the above configuration is usually provided on a substrate.
  • the order of the layers to be formed, the number of layers, and the thickness of each layer can be appropriately set in consideration of luminous efficiency and lifetime.
  • the organic EL element is usually provided on the substrate with the anode disposed on the substrate side, but may be disposed on the substrate with the cathode disposed on the substrate side.
  • the layers are laminated on the substrate in order from the anode side (left side of each configuration a to k).
  • the organic EL element may be a bottom emission type that emits light from the substrate side or a top emission type that emits light from the side opposite to the substrate.
  • a substrate that is not chemically changed is preferably used in the manufacturing process of the organic EL element.
  • a rigid substrate such as a glass substrate or a silicon substrate may be a flexible substrate such as a plastic substrate or a polymer film. There may be.
  • a flexible substrate it can be set as a flexible organic EL element as a whole, and an organic EL element can be formed by a roll-to-roll system.
  • An electrode and a drive circuit for driving the organic EL element may be formed in advance on the substrate.
  • an electrode having optical transparency is used for the anode.
  • the electrode exhibiting light transmittance a thin film of metal oxide, metal sulfide, metal or the like having high electrical conductivity can be used, and a thin film having high light transmittance is preferably used.
  • a thin film made of indium oxide, zinc oxide, tin oxide, ITO, indium zinc oxide (abbreviated as IZO), gold, platinum, silver, copper, or the like is used.
  • ITO, IZO, or oxidation is used.
  • a thin film made of tin is preferably used.
  • anode forming method examples include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method.
  • an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof may be used as the anode.
  • a material that reflects light may be used for the anode, and the material is preferably a metal, metal oxide, or metal sulfide having a work function of 3.0 eV or more.
  • the thickness of the anode can be appropriately determined in consideration of light transmittance, electrical conductivity, and the like.
  • the thickness of the anode is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
  • hole injection materials constituting the hole injection layer include oxides such as vanadium oxide, molybdenum oxide, ruthenium oxide, and aluminum oxide, phenylamine compounds, starburst amine compounds, phthalocyanine compounds, amorphous carbon, polyaniline And polythiophene derivatives such as polyethylenedioxythiophene (PEDOT).
  • oxides such as vanadium oxide, molybdenum oxide, ruthenium oxide, and aluminum oxide
  • PEDOT polyethylenedioxythiophene
  • the coating method described above using an ink containing a hole injection material may be used.
  • the hole injection layer may be formed by a predetermined known method different from the coating method.
  • the thickness of the hole injection layer varies depending on the material used, and is appropriately determined in consideration of the required characteristics and the ease of film formation.
  • the thickness of the hole injection layer is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • ⁇ Hole transport layer> There is no restriction
  • a formation method using a mixed liquid containing a polymer binder and a hole transport material can be exemplified.
  • a forming method by a coating method using an ink containing a hole transport material can be exemplified.
  • an organic thin film is formed by applying a coating solution containing a material having a crosslinkable group to form a coating film, and repeatedly irradiating the coating film with electromagnetic waves to crosslink the crosslinkable group.
  • a coating solution containing a material having a crosslinkable group to form a coating film
  • electromagnetic waves to crosslink the crosslinkable group.
  • the hole transport layer of the organic EL device of the present invention contains a hole transport material.
  • the hole transport material is not particularly limited as long as it is an organic compound having a hole transport function.
  • Specific examples of the organic compound having a hole transport function include polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine residue in a side chain or a main chain, a pyrazoline derivative, an arylamine derivative, a stilbene Derivative, triphenyldiamine derivative, polyaniline or derivative thereof, polythiophene or derivative thereof, polypyrrole or derivative thereof, polyarylamine or derivative thereof, poly (p-phenylene vinylene) or derivative thereof, polyfluorene derivative, aromatic amine residue And a polymer compound having poly (2,5-thienylene vinylene) or a derivative thereof.
  • the organic compound having a hole transport function is preferably a polymer compound such as a polymer. This is because when the organic compound having a hole transporting function is a polymer compound, the film formability is improved, and the light emitting property of the organic EL element can be made uniform.
  • the polystyrene-equivalent number average molecular weight of the organic compound having a hole transport function is 10,000 or more, preferably 3.0 ⁇ 10 4 to 5.0 ⁇ 10 5 , more preferably 6.0 ⁇ 10. 4 to 1.2 ⁇ 10 5 .
  • the weight average molecular weight in terms of polystyrene of the organic compound having a hole transport function is 1.0 ⁇ 10 4 or more, preferably 5.0 ⁇ 10 4 to 1.0 ⁇ 10 6 , more preferably. 1.0 ⁇ 10 5 to 6.0 ⁇ 10 5 .
  • organic compounds having a hole transport function include polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine residue in a side chain or a main chain, polyaniline or a derivative thereof, polythiophene Or a derivative thereof, a polyfluorene derivative, a polymer compound having an aromatic amine residue, poly (p-phenylene vinylene) or a derivative thereof, and a polymer hole such as poly (2,5-thienylene vinylene) or a derivative thereof Transport materials are preferred, more preferably polyvinyl carbazole or derivatives thereof, polysilane or derivatives thereof, polysiloxane derivatives having aromatic amine residues in the side chain or main chain, polyfluorene derivatives, and polymerisation having aromatic amine residues Thing is.
  • the organic compound having a hole transport function is a low molecule, it is preferably used by being dispersed in a polymer binder.
  • Polyvinylcarbazole or a derivative thereof, which is an organic compound having a hole transport function can be obtained, for example, by cationic polymerization of a vinyl monomer or radical polymerization.
  • polysilanes or derivatives thereof which are organic compounds having a hole transporting function
  • examples of polysilanes or derivatives thereof, which are organic compounds having a hole transporting function include compounds described in Chem. Rev. 89, 1359 (1989), GB GB2300196 published specification. Etc.
  • the synthesis method methods described in these documents can be used, and the Kipping method is particularly preferably used.
  • a compound having the structure of the low molecular hole transport material in the side chain or main chain is preferably used because the siloxane skeleton structure has almost no hole transport property.
  • compounds having a hole transporting aromatic amine residue in the side chain or main chain can be mentioned.
  • a polymer having a fluorenediyl group represented by the following formula (1) is preferable. This is because when the hole transport layer of the organic EL device is brought into contact with an organic compound having a condensed ring or a plurality of aromatic rings, the hole injection efficiency is improved and the current density during driving is increased.
  • R 1 and R 2 may be the same or different and each independently represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group.
  • the alkyl group include groups having 1 to 10 carbon atoms.
  • the alkoxy group include groups having 1 to 10 carbon atoms.
  • the aryl group include a phenyl group and a naphthyl group.
  • monovalent heterocyclic groups include pyridyl groups.
  • the aryl group and the monovalent heterocyclic group may have a substituent.
  • the substituent include an alkyl group having 1 to 10 carbon atoms and a carbon atom from the viewpoint of improving the solubility of the polymer compound. Examples thereof include an alkoxy group having 1 to 10 atoms.
  • the aryl group and the monovalent heterocyclic group may have a crosslinkable group as a substituent.
  • the crosslinkable group include vinyl group, ethynyl group, butenyl group, group having acrylic structure, group having acrylate structure, group having acrylamide structure, group having methacrylic structure, group having methacrylate structure, methacrylamide structure , A group having a vinyl ether structure, a vinylamino group, a group having a silanol structure, a group having a small ring (for example, cyclopropane, cyclobutane, epoxide, oxetane, diketene, episulfide, etc.).
  • a particularly preferable organic compound having a hole transport function is a polymer containing the fluorenediyl group and the structure of an aromatic tertiary amine compound as repeating units, for example, a polyarylamine polymer.
  • repeating unit including the structure of the aromatic tertiary amine compound examples include a repeating unit represented by the following formula (2).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent an arylene group or a divalent heterocyclic group.
  • Ar 5 , Ar 6 and Ar 7 each independently represents an aryl group or a monovalent heterocyclic group.
  • Ar 6 and Ar 7 may be combined to form a ring together with the nitrogen atom to which Ar 6 and Ar 7 are bonded.
  • m and n each independently represents 0 or 1.
  • arylene groups include phenylene groups.
  • divalent heterocyclic group include a pyridinediyl group. These groups may have a substituent.
  • Examples of the aryl group include a phenyl group and a naphthyl group.
  • Examples of the monovalent heterocyclic group include a pyridyl group. These groups may have a substituent.
  • Examples of monovalent heterocyclic groups include thienyl group, furyl group, pyridyl group and the like.
  • the substituent that the arylene group, aryl group, divalent heterocyclic group and monovalent heterocyclic group may have, from the viewpoint of the solubility of the polymer compound, an alkyl group, an alkoxy group, an aryl group Are preferable, and an alkyl group is more preferable.
  • the alkyl group include groups having 1 to 10 carbon atoms.
  • the alkoxy group include groups having 1 to 10 carbon atoms.
  • the aryl group include a phenyl group and a naphthyl group.
  • the substituent may have a crosslinkable group.
  • the crosslinkable group include vinyl group, ethynyl group, butenyl group, group having acrylic structure, group having acrylate structure, group having acrylamide structure, group having methacrylic structure, group having methacrylate structure, methacrylamide structure , A group having a vinyl ether structure, a vinylamino group, a group having a silanol structure, a group having a small ring (for example, cyclopropane, cyclobutane, epoxide, oxetane, diketene, episulfide, etc.).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are preferably arylene groups, and more preferably phenylene groups.
  • Ar 5 , Ar 6 and Ar 7 are preferably aryl groups, and more preferably phenyl groups.
  • the carbon atom in Ar 1 and the carbon atom in Ar 3 may be directly bonded, or through a divalent group such as a group represented by —O— or a group represented by —S—. May be combined.
  • m and n are preferably 0.
  • repeating unit represented by the formula (2) examples include a repeating unit represented by the following formula.
  • a crosslinker is further used as a material having a crosslinkable group.
  • the crosslinking agent include vinyl group, acetyl group, butenyl group, acrylic group, acrylamide group, methacryl group, methacrylamide group, vinyl ether group, vinylamino group, silanol group, cyclopropyl group, cyclobutyl group, epoxy group, oxetane.
  • a compound having a polymerizable substituent selected from the group consisting of a group, a diketene group, an episulfide group, a lactone group, and a lactam group.
  • a polyfunctional acrylate is preferable, and examples thereof include dipentaerythritol hexaacrylate (DPHA) and trispentaerythritol octaacrylate (TPEA).
  • DPHA dipentaerythritol hexaacrylate
  • TPEA trispentaerythritol octaacrylate
  • the method of forming a positive hole transport layer When the organic compound which has a positive hole transport function is a low molecule, the method by the film-forming using a mixed solution with a polymer binder is mentioned. In the case where the organic compound having a hole transporting function is a polymer, a film forming method using a solution may be used.
  • the solvent used for film formation using a solution is not particularly limited as long as it can dissolve a hole transport material.
  • the solvent include chloride solvents such as chloroform, methylene chloride and dichloroethane, ether solvents such as tetrahydrofuran, aromatic hydrocarbon solvents such as toluene and xylene, ketone solvents such as acetone and methyl ethyl ketone, ethyl acetate, butyl acetate and ethyl.
  • Examples include ester solvents such as cellosolve acetate.
  • the coating method described above can be cited.
  • the polymer binder used in the mixed solution a binder that does not excessively inhibit charge transport is preferable, and a binder that absorbs less visible light is preferably used.
  • the polymer binder include polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.
  • the thickness of the hole transport layer varies depending on the material used and may be selected so that the drive voltage and the light emission efficiency are appropriate values.
  • the hole transport layer needs to have a thickness that does not generate pinholes. If the hole transport layer is too thick, the driving voltage of the organic EL element may be increased.
  • the thickness of the hole transport layer is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • the light emitting layer usually contains an organic substance that mainly emits fluorescence and / or phosphorescence, or an organic substance and a dopant that assists the organic substance.
  • the dopant is added, for example, to improve the luminous efficiency or change the emission wavelength.
  • the organic substance is preferably a polymer compound from the viewpoint of solubility.
  • the light emitting layer preferably contains a polymer compound having a polystyrene-equivalent number average molecular weight of 10 3 to 10 8 .
  • Examples of the light emitting material constituting the light emitting layer include the following dye materials, metal complex materials, polymer materials, and dopant materials.
  • dye materials include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds, pyridine rings.
  • examples thereof include compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, oxadiazole dimers, pyrazoline dimers, quinacridone derivatives, and coumarin derivatives.
  • Metal complex materials examples include rare earth metals such as Tb, Eu, and Dy, or Al, Zn, Be, Pt, Ir, and the like as a central metal, and an oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, and quinoline structure. And the like.
  • metal complexes include metal complexes having light emission from triplet excited states such as iridium complexes and platinum complexes, aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, A porphyrin zinc complex, a phenanthroline europium complex, etc. can be mentioned.
  • Polymer material examples include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, materials obtained by polymerizing the above dye materials and metal complex materials, and the like. Can be mentioned.
  • Dopant material examples include perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squalium derivatives, porphyrin derivatives, styryl dyes, tetracene derivatives, pyrazolone derivatives, decacyclene, and phenoxazone.
  • the thickness of the light emitting layer is usually about 2 nm to 200 nm.
  • the light emitting layer can be formed by a coating method using an ink containing a light emitting material as described above.
  • a known material can be used as the electron transport material constituting the electron transport layer.
  • an electron transport material constituting the electron transport layer an oxadiazole derivative, anthraquinodimethane or a derivative thereof, benzoquinone or a derivative thereof, naphthoquinone or a derivative thereof, anthraquinone or a derivative thereof, tetracyanoanthraquinodimethane or a derivative thereof, Fluorenone derivatives, diphenyldicyanoethylene or derivatives thereof, diphenoquinone derivatives, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof, polyfluorene or derivatives thereof, and the like can be given.
  • electron transport materials include oxadiazole derivatives, benzoquinone or derivatives thereof, anthraquinones or derivatives thereof, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof, polyfluorenes Or a derivative thereof, preferably 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum, and polyquinoline. preferable.
  • examples of the method for forming the electron transport layer include a vacuum deposition method using powder, film formation from a solution or a molten state, and a polymer electron transport material.
  • film formation from a solution or a molten state can be mentioned.
  • the thickness of the electron transport layer varies depending on the material used, and is appropriately determined in consideration of the required characteristics and the ease of film formation.
  • the thickness of the electron transport layer is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • ⁇ Electron injection layer> As the material constituting the electron injection layer, an optimum material is appropriately selected according to the type of the light emitting layer.
  • Examples of the material constituting the electron injection layer include alkali metals, alkaline earth metals, alloys containing at least one of alkali metals and alkaline earth metals, oxides of alkali metals or alkaline earth metals, halides , Carbonates, or mixtures of these substances.
  • alkali metals, alkali metal oxides, alkali metal halides, and alkali metal carbonates include lithium, sodium, potassium, rubidium, cesium, lithium oxide, lithium fluoride, sodium oxide, sodium fluoride, Examples include potassium oxide, potassium fluoride, rubidium oxide, rubidium fluoride, cesium oxide, cesium fluoride, and lithium carbonate.
  • alkaline earth metals, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal carbonates include magnesium, calcium, barium, strontium, magnesium oxide, magnesium fluoride, Examples thereof include calcium oxide, calcium fluoride, barium oxide, barium fluoride, strontium oxide, strontium fluoride, and magnesium carbonate.
  • the electron injection layer may be composed of a laminate in which two or more layers are laminated, and examples thereof include a laminate of a LiF layer and a Ca layer.
  • the electron injection layer can be formed by a predetermined known method such as an evaporation method, a sputtering method, or a printing method.
  • the thickness of the electron injection layer is preferably about 1 nm to 1 ⁇ m.
  • a material for the cathode is preferably a material having a low work function, easy electron injection into the light emitting layer, and high electrical conductivity.
  • the cathode material is a visible light reflectance. High material is preferred.
  • the material of the cathode for example, alkali metal, alkaline earth metal, transition metal, Group 13 metal of the periodic table, and the like can be used.
  • cathode material examples include lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like.
  • An alloy, graphite, or a graphite intercalation compound is used.
  • alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, calcium-aluminum alloys, and the like.
  • a transparent conductive electrode made of a conductive metal oxide, a conductive organic material, or the like can be used.
  • the conductive metal oxide include indium oxide, zinc oxide, tin oxide, ITO, and IZO.
  • the conductive organic substance include polyaniline or a derivative thereof, polythiophene or a derivative thereof, and the like. be able to.
  • the cathode may be composed of a laminate in which two or more layers are laminated. In some cases, the electron injection layer is used as a cathode.
  • the thickness of the cathode is appropriately set in consideration of electric conductivity and durability.
  • the thickness of the cathode is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
  • Examples of the method for forming the cathode include a vacuum deposition method, a sputtering method, and a laminating method in which a metal thin film is thermocompression bonded.
  • the organic EL element of the present embodiment described above can be suitably used for a curved or flat illumination device, for example, a planar light source used as a light source of a scanner, and a display device.
  • Organic photoelectric conversion elements are classified into two types, bulk heterojunction type and heterojunction type, from the configuration of an active layer (sometimes referred to as an organic semiconductor layer).
  • the method for producing an electronic device of the present invention can be applied to any kind of organic photoelectric conversion element.
  • the organic photoelectric conversion element is basically composed of a pair of electrodes, at least one of which is transparent or translucent, and a single layer composed of an organic thin film in the case of a bulk heterojunction type disposed between the pair of electrodes.
  • a heterojunction type it has a laminated structure including two active layers made of an organic thin film.
  • the substrate, the electrode, the active layer, and other components that are formed as necessary, which constitute the organic photoelectric conversion element, will be described.
  • the organic photoelectric conversion element usually has a configuration in which the above layers are stacked on a substrate including a rigid substrate and a flexible substrate.
  • the substrate may be any substrate as long as it can form electrodes and does not change chemically when forming an organic thin film, and can be the same substrate that can be used for the organic EL element.
  • At least one of the pair of electrodes is made of a transparent or translucent electrode material.
  • the electrode opposite to the opaque substrate side is transparent or translucent.
  • the transparent or translucent electrode material include a conductive metal oxide film, a translucent metal thin film, and the like.
  • transparent or translucent electrode materials include, specifically, films made of conductive materials such as indium oxide, zinc oxide, tin oxide, ITO, IZO, NESA, gold, platinum, silver, Examples include a film using copper or the like. Of these, ITO, IZO and tin oxide films are preferable.
  • the other may be an opaque electrode.
  • an opaque electrode material a metal, a conductive polymer, or the like can be used.
  • opaque electrode materials include lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, etc.
  • a metal selected from the group consisting of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, and tin.
  • Examples thereof include alloys with the above metals, graphite, graphite intercalation compounds, polyaniline and derivatives thereof, and polythiophene and derivatives thereof.
  • Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy and the like.
  • Examples of methods for producing these electrodes include vacuum deposition, sputtering, ion plating, and plating. Moreover, you may use organic transparent conductive films, such as polyaniline and its derivative (s), polythiophene, and its derivative (s) as an electrode material.
  • the transparent or translucent electrode may be an anode or a cathode.
  • the active layer included in the organic photoelectric conversion element includes an electron donating compound and an electron accepting compound in the case of a bulk heterojunction type, and an electron accepting compound and a layer including an electron donating compound in the case of a heterojunction type.
  • the containing layer is joined.
  • the electron donating compound is not particularly limited.
  • electron donating compounds include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, oligothiophenes and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilanes and derivatives thereof, aromatic amines in the side chain or main chain And polysiloxane derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polymer compounds having thiophene as a partial skeleton, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, and polythienylene vinylene and derivatives thereof.
  • Examples of the electron-accepting compound include a compound having a benzothiadiazole structure, a polymer compound having a benzothiadiazole structure in a repeating unit, a compound having a quinoxaline structure, a polymer compound having a quinoxaline structure in a repeating unit, titanium oxide, carbon nanotube, and fullerene A fullerene derivative is preferred.
  • the active layer may contain components other than those described above in order to express various functions.
  • components other than the above include ultraviolet absorbers, antioxidants, sensitizers for sensitizing the function of generating charges by absorbed light, and light stabilizers for increasing stability from ultraviolet rays. It is done.
  • the active layer may contain a polymer compound other than the electron donating compound and the electron accepting compound as a polymer binder in order to enhance mechanical properties.
  • a polymer binder a binder that does not excessively inhibit the electron transporting property or hole transporting property and a binder that absorbs less visible light are preferably used.
  • polymer binders examples include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof , Polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.
  • the active layer having the above-described configuration is formed using a solution containing an electron-donating compound, an electron-accepting compound, and other components blended as necessary. Can be formed.
  • an active layer can be formed by applying this solution on an anode or a cathode.
  • the solvent used for film formation using the solution may be any solvent that dissolves the above-described electron-donating compound and electron-accepting compound, and a plurality of solvents may be mixed.
  • the solvent include unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, diethylene
  • Halogenated saturated hydrocarbon solvents such as chloropropane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and trich
  • the organic thin film is formed by applying a coating liquid containing a material having a crosslinkable group to form a coating film, and repeatedly irradiating the coating film with electromagnetic waves to crosslink the crosslinkable group.
  • the predetermined layer including the active layer can be formed by the step of forming the layer.
  • a material having the above-described crosslinkable group as a substituent or the above-described crosslinker can be used as the material having a crosslinkable group.
  • the organic photoelectric conversion element has an additional intermediate layer (buffer layer, charge transport layer, etc.) other than the active layer in order to improve the photoelectric conversion efficiency. May be included.
  • Such an intermediate layer can be provided, for example, between the anode and the active layer, or between the cathode and the active layer.
  • Examples of materials used for the intermediate layer include alkali metal or alkaline earth metal halides or oxides such as lithium fluoride.
  • the material of the intermediate layer includes fine particles of inorganic semiconductor such as titanium oxide, a mixture of PEDOT (poly (3,4-ethylenedioxythiophene)) and PSS (poly (4-styrenesulfonate)) (PEDOT: PSS). ) Etc. may be used.
  • Organic thin film transistor examples include a source electrode and a drain electrode, an active layer including a polymer compound of the present invention that serves as a current path between these electrodes, and a gate electrode that controls the amount of current passing through the current path.
  • the transistor which has the structure mentioned above is mentioned.
  • Examples of the organic thin film transistor having such a configuration include a field effect organic thin film transistor and a static induction organic thin film transistor.
  • a field effect organic thin film transistor generally includes a source electrode and a drain electrode, an active layer containing a polymer compound serving as a current path between these electrodes, a gate electrode for controlling the amount of current passing through the current path, and an active layer And an insulating layer disposed between the gate electrode and the gate electrode.
  • An electrostatic induction type organic thin film transistor usually has a source electrode and a drain electrode, an active layer containing a polymer compound serving as a current path between these electrodes, and a gate electrode for controlling the amount of current passing through the current path.
  • the gate electrode is provided in the active layer.
  • the gate electrode only needs to have a structure in which a current path flowing from the source electrode to the drain electrode can be formed and the amount of current flowing through the current path can be controlled by a voltage applied to the gate electrode.
  • Type electrode
  • the field effect organic thin film transistor can be manufactured by a known method, for example, a method described in JP-A-5-110069.
  • the electrostatic induction organic thin film transistor can be produced by a known method such as the method described in JP-A-2004-006476.
  • the organic thin film transistor is usually formed on a substrate including a rigid substrate and a flexible substrate.
  • the material of the substrate is not particularly limited as long as the material does not hinder the characteristics of the organic thin film transistor.
  • a substrate material a substrate similar to the substrate that can be used for the organic EL element can be used.
  • the material of the insulating layer may be any material having high electrical insulation, and SiO x , SiN x , Ta 2 O 5 , polyimide, polyvinyl alcohol, polyvinyl phenol, organic glass, photoresist, and the like can be used. Since the operating voltage can be lowered, it is preferable to use a material having a high dielectric constant.
  • ⁇ Gate electrode> a material such as gold, platinum, silver, copper, chromium, palladium, aluminum, indium, molybdenum, low-resistance polysilicon, low-resistance amorphous silicon, etc., tin oxide, indium oxide, ITO, etc. should be used. Can do. These materials may be used alone or in combination of two or more. Note that a silicon substrate doped with an impurity at a high concentration may be used as the gate electrode.
  • the source electrode and the drain electrode are preferably made of a low-resistance material, and particularly preferably made of gold, platinum, silver, copper, chromium, palladium, aluminum, indium, molybdenum or the like. These materials may be used alone or in combination of two or more.
  • ⁇ Other layers> In the organic thin film transistor, a layer composed of another compound may be interposed between the source and drain electrodes and the active layer.
  • Such layers include low molecular compounds with electron transport properties, low molecular compounds with hole transport properties, alkali metals, alkaline earth metals, rare earth metals, complexes of these metals with organic compounds, iodine, bromine.
  • Halogens such as chlorine and iodine chloride, sulfur oxide compounds such as sulfuric acid, sulfuric anhydride, sulfur dioxide and sulfate, nitric oxide compounds such as nitric acid, nitrogen dioxide and nitrate, halogenated compounds such as perchloric acid and hypochlorous acid , Alkyl thiol compounds, aromatic thiols, and layers made of aromatic thiol compounds such as fluorinated alkyl aromatic thiols.
  • a protective film is preferably formed on the organic thin film transistor in order to protect the organic thin film transistor.
  • an organic thin-film transistor is interrupted
  • the influence on the organic thin-film transistor in the formation process can also be reduced by this protective film.
  • the method for forming the protective film include a method of covering the organic thin film transistor with a film made of UV curable resin, thermosetting resin, or SiON X.
  • the predetermined layer including the semiconductor layer and the insulating layer is formed by applying a coating solution containing a material having a crosslinkable group to form a coating film, and repeatedly irradiating the coating film with electromagnetic waves to crosslink the crosslinkable group.
  • the organic thin film can be formed by the step of forming the organic thin film.
  • the material having a crosslinkable group used at that time the above-described material having the crosslinkable group as a substituent or the above-mentioned crosslinker can be used.
  • the filters used in Examples 1 to 3 described later will be described with reference to FIGS. 1 and 2 are graphs showing the characteristics of the filter.
  • the used filter is a filter called a sharp cut filter, and has a function of absorbing only light having a wavelength shorter than a predetermined wavelength and transmitting only light having a wavelength longer than the predetermined wavelength.
  • the sharp cut filter has a wavelength slope that is the distance between the wavelength value at which the transmittance is 72% (high transmission limit wavelength) and the wavelength value at which the transmittance is 5% (absorption limit wavelength) in the spectral transmittance. It is characterized by the transmission limit wavelength, which is the value of the wavelength corresponding to the point.
  • the transmission limit wavelength of S76-L37 (trade name) is 370 (nm)
  • the transmission limit wavelength of S76-L42 is 420 (nm).
  • the transmission limit wavelength of S76-Y52 is 520 (nm).
  • the reaction vessel was heated to 100 ° C., 7.4 mg of palladium (II) acetate, 70 mg of tri (o-tolyl) phosphine, and 64 g of an about 18% by mass sodium carbonate aqueous solution were added, and the stirring was continued for 3 hours or more. It was. Thereafter, 400 mg of phenylboronic acid was added, and heating and stirring were further continued for 5 hours.
  • the reaction solution was diluted with 1900 g of toluene, washed twice with 60 g of a 3% by mass aqueous acetic acid solution, and further washed once with 60 g of ion-exchanged water. ) Was added and stirred for 4 hours.
  • the resulting solution was purified by column chromatography using an equal volume mixture of alumina and silica gel as the stationary phase.
  • the obtained toluene solution was dropped into methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain polymer compound 1 composed of a repeating unit represented by the following formula (6).
  • the number given to each repeating unit represents the composition ratio of each repeating unit in the polymer compound 1.
  • the obtained polymer compound 1 had a polystyrene-equivalent number average molecular weight of 8.9 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 4.2 ⁇ 10 5 .
  • Example 1 An organic EL device having the following configuration was produced. “Glass substrate / ITO layer (thickness 50 nm) / layer containing PEDOT (thickness 65 nm) / layer containing polymer compound 1 (thickness 20 nm) / layer containing polymer compound 2 (thickness 80 nm) / NaF layer (Thickness 4 nm) / Al layer (thickness 100 nm) "
  • the layer containing PEDOT corresponds to a hole injection layer
  • the layer containing polymer compound 1 corresponds to a hole transport layer
  • the layer containing polymer compound 2 corresponds to a light emitting layer.
  • a suspension of poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT: Bayer, trade name “BaytronP AI4083”) was filtered through a 0.2 ⁇ m membrane filter to obtain a filtrate.
  • This filtrate was applied by spin coating to a glass substrate on which an ITO film (anode) having a thickness of 50 nm was formed by sputtering. Thereafter, a hole injection layer having a thickness of 65 nm was obtained by heat treatment at 200 ° C. for 20 minutes. The hole injection layer was formed in an air atmosphere.
  • a xylene solution in which the polymer compound 1 obtained by the above synthesis example was dissolved in xylene was prepared.
  • the concentration of the polymer compound 1 in this xylene solution was 0.5% by weight.
  • the obtained xylene solution was applied to a glass substrate by a spin coating method to form a coating film for a hole transport layer having a thickness of 20 nm.
  • a sharp cut filter S76-Y52 manufactured by Suruga Seiki was placed on the glass substrate in an air atmosphere, and the coating film was repeatedly irradiated with electromagnetic waves using the RC801 flash lamp manufactured by Xenon through the filter.
  • the irradiation time is 180 seconds, and the energy of one pulse is 3.68 J / cm 2 (in addition, an electromagnetic wave having an energy of one pulse of 207 J is applied to a 7.5 cm square region).
  • the pulse width was 168 ⁇ s and the frequency was 10 Hz.
  • a thin film (organic thin film) solidified by crosslinking reaction of the crosslinkable group of the polymer compound 1 in the coating film was obtained, and a hole transport layer was obtained.
  • a xylene solution in which the polymer compound 2 as a light emitting material was dissolved in xylene was prepared.
  • the concentration of the polymer compound 2 in the xylene solution was 1.3% by weight.
  • the obtained xylene solution was applied to a glass substrate by a spin coating method to form a coating film for a light emitting layer having a thickness of 80 nm.
  • the coating film was dried by holding at 170 ° C. for 10 minutes to obtain a light emitting layer.
  • sodium fluoride (NaF) was vapor-deposited with a thickness of about 4 nm
  • aluminum (Al) was vapor-deposited with a thickness of about 100 nm to form a cathode.
  • sealing was performed using a glass substrate which is a sealing substrate, thereby producing an organic EL element.
  • the current efficiency of the produced organic EL element was measured. As a result, a maximum current efficiency of 11 cd / A was obtained.
  • Example 2 an organic EL device was formed in the same manner as in Example 1 except that the sharp cut filter used during irradiation with the flash lamp was changed in forming the layer containing the polymer compound 1. Specifically, in Example 2, a sharp cut filter S76-L42 was used.
  • the current efficiency of the produced organic EL element was measured. As a result, a maximum current efficiency of 11 cd / A was obtained.
  • Example 3 an organic EL device was formed in the same manner as in Example 1 except that the sharp cut filter used for irradiation with the flash lamp was changed in forming the layer containing the polymer compound 1. Specifically, in Example 3, a sharp cut filter S76-L37 was used.
  • Example 4 an organic EL device was formed in the same manner as in Example 1 except that the sharp cut filter was not used in forming the layer containing the polymer compound 1.
  • an organic EL element was formed in the same manner as in Example 1 except that a hot plate was used instead of the flash lamp in forming the layer containing the polymer compound 1.
  • a xylene solution in which the polymer compound 1 is dissolved in xylene is applied to a glass substrate by spin coating in an air atmosphere to form a coating film for a hole transport layer having a thickness of 20 nm. did.
  • the obtained coating film was made into a thin film that was solidified by holding at 180 ° C. for 60 minutes in an air atmosphere to obtain a hole transport layer.
  • Polymer compound 1 was dissolved in xylene to prepare xylene solution 1.
  • concentration of the polymer compound 1 in the xylene solution 1 was 0.5% by weight.
  • the xylene solution 1 was applied to a glass substrate by a spin coating method to obtain a coating film of the polymer compound 1.
  • Table 1 shows the equipment used in Examples 1 to 4 and the comparative examples, conditions, filters, and measured values of the remaining film ratio (%) and maximum current efficiency (cd / A).
  • Example 5 In an air atmosphere, a xylene solution in which the polymer compound 1 was dissolved in xylene was applied to a glass substrate by a spin coating method to form a coating film for a hole transport layer having a thickness of 20 nm. Next, in a N 2 atmosphere, a Xenon 370 nm or less cut filter (Type A) was placed on the glass substrate, and the coating film was repeatedly irradiated with electromagnetic waves using the Xenon RC801 flash lamp through the filter. . As a result, a thin film (organic thin film) solidified by crosslinking reaction of the crosslinkable group of the polymer compound 1 in the coating film was obtained, and a hole transport layer was obtained.
  • a Xenon 370 nm or less cut filter Type A
  • Example 5 only the electromagnetic wave irradiation conditions are different from each other. However, the total irradiation energy of electromagnetic waves was the same, and the frequency was 10 Hz.
  • Table 2 shows the electromagnetic wave irradiation conditions of each example. In Table 2, the percentage display of the values of the pulse peak energy, energy / pulse, pulse width, and LT 70 of each example indicates the percentage when the value of Example 5 is used as a reference (100%).
  • LT70 means the time until the luminance becomes 70% of the initial luminance when driven at a constant current with an initial luminance of 5000 cd / m 2 .
  • Each of Examples 5 to 9 shows that the energy intensity per pulse can be reduced, suggesting that the influence of heat on the substrate and other layers can be reduced. Therefore, the production method of the present invention can be more suitably applied to the roll-to-roll method.
  • the remaining film ratio equal to or higher than that of the comparative example was achieved. Therefore, according to the production method of the present invention, it was suggested that even when another functional layer is formed as an upper layer by a coating method, dissolution of the lower layer thin film by the solvent for forming the upper layer can be effectively suppressed.

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Abstract

Afin d'empêcher tout endommagement d'un substrat ou d'électrodes fournies au préalable et d'une couche fonctionnelle lorsqu'une couche mince est formée au moyen d'un procédé d'enrobage, le procédé de fabrication selon la présente invention d'un dispositif électronique qui est doté de deux électrodes ou plus et d'une couche mince organique qui est prévue entre les deux électrodes ou plus, inclut une étape au cours de laquelle un liquide de revêtement qui contient un matériau qui est doté d'un groupe réticulable est appliqué de manière à former un film de protection, et une étape au cours de laquelle le groupe réticulable est réticulé en exposant de façon répétée le film de protection à des ondes électromagnétiques, ce qui permet de la sorte de former la couche mince organique.
PCT/JP2013/077246 2012-10-15 2013-10-07 Procédé permettant de fabriquer un dispositif électronique Ceased WO2014061493A1 (fr)

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US14/434,518 US9437821B2 (en) 2012-10-15 2013-10-07 Method for manufacturing electronic device

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US9437821B2 (en) 2016-09-06
EP2908608A4 (fr) 2016-06-29
JP2014099392A (ja) 2014-05-29
US20150280126A1 (en) 2015-10-01
EP2908608B1 (fr) 2019-11-20
CN104718798A (zh) 2015-06-17
EP2908608A1 (fr) 2015-08-19
CN104718798B (zh) 2017-09-05

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